WO1994006806A1 - Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes - Google Patents

Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes Download PDF

Info

Publication number
WO1994006806A1
WO1994006806A1 PCT/US1993/008675 US9308675W WO9406806A1 WO 1994006806 A1 WO1994006806 A1 WO 1994006806A1 US 9308675 W US9308675 W US 9308675W WO 9406806 A1 WO9406806 A1 WO 9406806A1
Authority
WO
WIPO (PCT)
Prior art keywords
silane
methyl
ketoximino
tris
methyl isobutyl
Prior art date
Application number
PCT/US1993/008675
Other languages
English (en)
French (fr)
Inventor
Chempolil Thomas Mathew
Edward Thanaraj Asirvatham
Jeffrey Alan Knepper
Dale Russel Flackett
Original Assignee
Allied-Signal Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Allied-Signal Inc. filed Critical Allied-Signal Inc.
Priority to DE69308579T priority Critical patent/DE69308579T2/de
Priority to EP93921570A priority patent/EP0660838B1/en
Publication of WO1994006806A1 publication Critical patent/WO1994006806A1/en
Priority to GR970401213T priority patent/GR3023562T3/el

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0892—Compounds with a Si-O-N linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/04—Esters of silicic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups

Definitions

  • a variety of useful silicone compositions cure at room temperature to elastomeric materials which possess a broad spectrum of physical and chemical properties.
  • compositions are particularly desirable because they surface cure in thirty minutes or less after exposure to the atmosphere but remain substantially soft for years. They also adhere tenaciously to a wide variety of materials such as glass, porcelain, wood, metal and organic plastics. Because of this, they are adaptable for practically any type of sealant application including building and automotive equipment applications. The following patents discuss some of these compounds in more detail.
  • U.S. Patent 3,189,576 to Sweet describes oxime silanes useful in the manufacture of room temperature curing compositions. Specifically, Sweet teaches trifunctional and tetrafunctional ketoximino silanes as crosslinkers and their use in the manufacture of room temperature curing silicone elastomeric compositions by mixing them with hydroxyl endblocked polydiorganosiloxanes. These compositions can also contain fillers and curing catalysts.
  • U.S. Patent 4,503,210 to Von Au discloses mixtures of tri- and tetrafunctional ketoximino silanes and focuses specifically on the usefulness of tetrafunctional ketoximino silanes in sealant formulations.
  • tetrafunctional oximino silanes i.e., e.g., those based on methyl ethyl ketoxi e (MEKO) and acetone oxime
  • MEKO methyl ethyl ketoxi e
  • acetone oxime a compound that has a poor shelf life and require special care in their packaging and transporting.
  • the invention relates to silanes of the formula: where R is any saturated straight chain or branched alkyl radical of 1 to 7 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl and amyl, R 1 is any saturated, straight chain alkyl radical of 1 to 5 carbon atoms such as methyl, ethyl and propyl or an alkenyl radical of 1 to 5 carbon atoms such as methyl, vinyl and allyl and a is a positive integer ranging in value from 2 to 4.
  • the invention relates to the following silanes: methyl vinyl bis- (methyl isobutyl ketoximino) silane; methyl vinyl bis-(methyl amyl ketoximino) silane; methyl tris-(methyl isobutyl ketoximino) silane; vinyl tris-(methyl isobutyl ketoximino) silane; methyl tris-(methyl amyl ketoximino) silane; vinyl tris-(methyl amyl ketoximino) silane; tetrakis-(methyl isobutyl ketoximino) silane; tetrakis- (methyl amyl ketoximino) silane and mixtures thereof.
  • solubility limits the level of tetrafunctional oximino silane in the trifunctional oximino silane to 35 - 40% at room temperature. This is disadvantageous because higher levels of tetrafunctional oximino silane increase cure rate and minimize (if not eliminate) the need for a catalyst.
  • solid tetrafunctional oximino silanes are mixed with hydrocarbons like toluene, benzene and xylene, organic ethers like diethylether and dibutylether, ketones and halogenated solvents to facilitate ease of handling in applications which require precise amounts of tetrafunctional oximino silane. Because some of these solvents are flammable and carcinogenic, further precautions must be taken to ensure the safety of personnel during processing. In addition, one must ensure that the vapor emissions from the finished sealant products generated during end use are safe for people and the environment. These precautions are both costly and time consuming.
  • Solubility is also a concern. That is, for example, at room temperature, tetrafunctional MEKO-based silane is only 50% soluble in toluene and in methyl ethyl ketoxime, 40% soluble in diethyl ether and 10% soluble in dibutyl ether. As a result, significant amounts of solvent may be required in the formulation. In addition, crystallization can occur at lower temperatures (i.e., e.g., during shipping in winter months) and at higher concentrations of the tetrafunctional oximino silane.
  • novel ketoximino silanes of the invention may be prepared by following the syntheses outlined below. See, U.S. Patent 4,400,527. Alternately, they may be prepared by any means known in the art. We note that the oximes used in the syntheses below may be prepared by any means known in the art. See, for example, the syntheses outlined in U.S. Patents 4,163,756 and 3,991,115 both to Allied-Signal Inc.
  • a 1 liter 3-necked flask equipped with a condenser, thermometer and dropping funnel was charged with 350 ml. of hexane and 96.7g (0.84 mol) of distilled methyl isobutyl ketoxime.
  • a drierite tube was attached to the condenser to ensure a dry reaction medium.
  • the reaction flask was then placed in a cold water bath. While the hexane/ketoxi e solution was stirred using a magnetic stirrer, 17g (0.1 mol) tetrachloro silane was added dropwise into the reaction flask. The reaction temperature was maintained between 35 and 42°C during the addition.
  • the top phase was separated from the methyl isobutyl ketoxime hydrochloride bottom phase using a separatory funnel and neutralized with ammonia gas by bubbling the ammonia through the liquid for 10 minutes.
  • Solid ammonium chloride was filtered off and hexane was removed from the filtrate by vacuum distillation to give 380 g (98.7%) of a colorless liquid.
  • the identity of the product as methyl tris-(methyl isobutyl ketoximino) silane was confirmed by IR and proton and carbon-13 NMR spectral data.
  • the top phase containing product and hexane was separated from the bottom phase (methyl isobutyl ketoxime hydrochloride) using a separatory funnel and neutralized with ammonia gas for 10-15 minutes. Solid ammonium chloride was filtered off and hexane was removed from the filtrate by distilling under reduced pressure to give 374 g (94%) of a colorless liquid. The identity of this liquid as vinyl tris- (methyl isobutyl ketoximino) silane was confirmed by IR and proton and carbon-13 NMR spectral data.
  • the top phase was neutralized with ammonia gas by bubbling the ammonia through the liquid for 10 minutes.
  • Solid ammonium chloride was filtered off and hexane was removed from the filtrate by distillation under reduced pressure to give 201.8 g (94.5%) of a colorless liquid.
  • This liquid was identified by IR and proton and carbon-13 NMR spectral data as methyl tris-(methyl amyl ketoximino) silane.
  • the top phase containing product and hexane was separated from the heavy bottom phase (methyl amyl ketoxime hydrochloride) using a separatory funnel and neutralized with ammonia gas by bubbling the ammonia through the liquid for 10 minutes.
  • Ammonium chloride was filtered to give a clear filtrate.
  • Hexane was removed from the filtrate by distilling under reduced pressure to give 115 g (87%) of a colorless liquid which was identified as vinyl tris- (methyl amyl ketoximino) silane by IR and proton and carbon-13 NMR spectral data.
  • the top phase was neutralized with ammonia gas by bubbling the ammonia through the liquid for 10 minutes and the precipitated ammonium chloride was filtered off. Hexane from the filtrate was removed by distillation under reduced pressure to give 27.5 g (89%) of a colorless liquid which was identified as methyl vinyl bis-(methyl isobutyl ketoximino) silane by IR and proton and carbon-13 NMR spectral data.
  • Ammonium chloride solid was filtered and hexane was removed from the filtrate by distillation under reduced pressure to give 286 g (87.7%) of a colorless liquid.
  • This liquid was identified as methyl vinyl bis- (methyl amyl ketoximino) silane by IR and proton and carbon-13 NMR spectral data.
  • hydroxy1 terminated polydimethylsiloxane HTPDMS
  • methyl tris-(methyl isobutyl ketoximino) silane prepared in accordance with the synthesis disclosed herein was added.
  • the compounds were mixed at 25°C at 200 rpm using a standard laboratory stirrer for 5 minutes.
  • the resulting product cured to a clear silicone rubber.
  • HTPDMS HTPDMS
  • 3 - 4 parts by weight of methyl tris-(methyl ethyl ketoximino) silane was added.
  • the compounds were mixed at 25°C and 200 rpm using a standard laboratory stirrer for 5 minutes.
  • the resulting product cured to an opaque, cloudy silicone rubber.
  • Comparative Example 1 The procedure outlined in Comparative Example 1 was repeated using the following silanes: l.) 2 - 10 parts by weight vinyl tris-(methyl ethyl ketoximino) silane; 2.) 3 - 10 parts by weight tetrakis-(methyl ethyl ketoximino) silane in toluene; 3.) 3:1 parts by weight of a mixture of methyl tris-(methyl ethyl ketoximino) silane and tetrakis-(methyl ethyl ketoximino) silane. The results are the same as those reported for Comparative Example 1. That is, the resulting product cured to an opaque, cloudy silicone rubber.
  • the silanes of the invention have utility as intermediates in the preparation of various one-component room-temperature-curing compositions for sealant, adhesive, coating and other silicone polymer applications.
  • These one-component systems may be prepared in accordance with the teachings of U.S. Patent 3,189,576 to Sweet (Example 17 at col. 12, lines 6 - 26) and U.S.. Patent 4,720,530 to Wur inghause et al. at col. 1, lines 60 - 67 and col. 2 , lines 1 - 43 which disclosure is hereby incorporated herein by reference.
  • the method for preparing one-component room-temperature- curing compositions comprises reacting in the substantial absence of moisture a hydroxy-endblocked siloxane polymer with a silane.
  • a silane such as silica, chalk and glass beads, adhesion promoters such as organofunctional silanes and catalysts such as tin carboxylates, dibutyl tin diacetate, and dibutyl tin dilaurate, lead carboxylates, zinc carboxylates and organo titanates may be included in these formulations.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/US1993/008675 1992-09-17 1993-09-14 Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes WO1994006806A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE69308579T DE69308579T2 (de) 1992-09-17 1993-09-14 Di-,tri- und tetrafunktionelle methyl-isobutyl und methyl-amyl ketoximosilanverbindungen
EP93921570A EP0660838B1 (en) 1992-09-17 1993-09-14 Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes
GR970401213T GR3023562T3 (en) 1992-09-17 1997-05-27 Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US947,015 1992-09-17
US07/947,015 US5359108A (en) 1992-09-17 1992-09-17 Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes

Publications (1)

Publication Number Publication Date
WO1994006806A1 true WO1994006806A1 (en) 1994-03-31

Family

ID=25485371

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/008675 WO1994006806A1 (en) 1992-09-17 1993-09-14 Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes

Country Status (9)

Country Link
US (2) US5359108A (da)
EP (1) EP0660838B1 (da)
JP (1) JP2554850B2 (da)
AT (1) ATE149500T1 (da)
DE (1) DE69308579T2 (da)
DK (1) DK0660838T3 (da)
ES (1) ES2098058T3 (da)
GR (1) GR3023562T3 (da)
WO (1) WO1994006806A1 (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014699A1 (en) * 1993-11-29 1995-06-01 Alliedsignal Inc. Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes
WO1995032240A1 (en) * 1994-05-24 1995-11-30 Alliedsignal Inc. Rtv silicone compositions using aminohydrocarbyl-substituted ketoximinosilanes

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3935133B2 (ja) * 2003-11-07 2007-06-20 本田技研工業株式会社 重畳部の形成方法
SI2225310T1 (sl) * 2007-12-28 2018-09-28 Nitrochemie Aschau Gmbh Polimeri, ki se dajo vulkanizirati pri sobni temperaturi
AU2012294839B2 (en) 2011-08-05 2016-06-30 Dow Corning Corporation Filled silicone compositions, preparations and uses thereof
JP5768674B2 (ja) * 2011-11-14 2015-08-26 信越化学工業株式会社 室温硬化性オルガノポリシロキサン組成物
CN111056970B (zh) * 2019-12-23 2022-10-18 浙江锦华新材料股份有限公司 一种丁酮肟盐酸盐中残留甲基三丁酮肟基硅烷的去除方法
CN111116411B (zh) * 2019-12-23 2022-10-18 浙江锦华新材料股份有限公司 一种去除丁酮肟盐酸盐中残留甲基三丁酮肟基硅烷的方法
EP4196532A1 (en) * 2020-08-13 2023-06-21 Soudal N.V. Silicone formulation comprising an oxime crosslinker, cured silicone formulation and uses thereof

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3189576A (en) 1962-09-07 1965-06-15 Dow Corning Organosilicon intermediates containing silicon-bonded oxime radicals
US3991115A (en) 1975-11-19 1976-11-09 Allied Chemical Corporation Process for the preparation of cyclohexanone oxime
US4033991A (en) * 1974-12-26 1977-07-05 Shin-Etsu Chemical Company, Limited Method for preparing organosilanes containing silicon-bonded oxime groups
US4163756A (en) 1978-04-11 1979-08-07 Allied Chemical Corporation Direct oximation of ketones
US4400527A (en) 1981-12-17 1983-08-23 Allied Corporation Producing oximinosilanes, oximinogermanes and oximinostannanes
US4503210A (en) 1983-02-03 1985-03-05 Wacker-Chemie Gmbh Oxime containing compositions which crosslink in the presence of moisture to form elastomers at room temperature
US4720530A (en) 1985-07-09 1988-01-19 Bayer Aktiengesellschaft RTV silicone pastes with a shortened hardening time
EP0369359A2 (de) * 1988-11-17 1990-05-23 Hüls Aktiengesellschaft Verfahren zur Herstellung von Ketoximosilanen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3826782A (en) * 1972-07-10 1974-07-30 Stauffer Chemical Co Room temperature curable organopolysiloxanes
DE3641756A1 (de) * 1986-12-06 1988-08-11 Huels Troisdorf Verfahren zur herstellung von ketoximosilanen
DE3903985A1 (de) * 1989-02-10 1990-08-16 Huels Chemische Werke Ag Verfahren zur herstellung von ketoximosilanen

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3189576A (en) 1962-09-07 1965-06-15 Dow Corning Organosilicon intermediates containing silicon-bonded oxime radicals
US4033991A (en) * 1974-12-26 1977-07-05 Shin-Etsu Chemical Company, Limited Method for preparing organosilanes containing silicon-bonded oxime groups
US3991115A (en) 1975-11-19 1976-11-09 Allied Chemical Corporation Process for the preparation of cyclohexanone oxime
US4163756A (en) 1978-04-11 1979-08-07 Allied Chemical Corporation Direct oximation of ketones
US4400527A (en) 1981-12-17 1983-08-23 Allied Corporation Producing oximinosilanes, oximinogermanes and oximinostannanes
US4503210A (en) 1983-02-03 1985-03-05 Wacker-Chemie Gmbh Oxime containing compositions which crosslink in the presence of moisture to form elastomers at room temperature
US4720530A (en) 1985-07-09 1988-01-19 Bayer Aktiengesellschaft RTV silicone pastes with a shortened hardening time
EP0369359A2 (de) * 1988-11-17 1990-05-23 Hüls Aktiengesellschaft Verfahren zur Herstellung von Ketoximosilanen

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 84, no. 7, 16 February 1976, Columbus, Ohio, US; abstract no. 44260y, SINGH, A. ET AL.: "ORGANOMETALLIC OXIMES AND ALLIED DERIVATIVES. V. PREPARATION AND CHARACTERIZATION OF SOME NEW TRIS(IMINOXY)ORGANOSILANES" page 517; *
CHEMICAL ABSTRACTS, vol. 92, no. 17, 28 April 1980, Columbus, Ohio, US; abstract no. 146832u, RUPANI, P. ET AL.: "SYNTHESIS AND CHARACTERIZATION OF SOME NEW ORGANO(IMINOXY)SILANES" page 600; *
GOEL, A.B. ET AL.: "UNTERSUCHUNGEN UBER DIE DIAMAGNETISCHE SUSZEPTIBILITAT EINIGER ORGANO(IMINO-OXY)SILANE", MONATSHEFTE FUR CHEMIE, vol. 107, no. 2, 1976, pages 531 - 535 *
INDIAN J. CHEM., vol. 13, no. 11, 1975, pages 1197 - 1199 *
SINGH, A. ET AL.: "SYNTHESIS AND CHARACTERISATION OF SOME ORGANO(IMINO-OXY)SILANES", JOURNAL OF THE CHEMICAL SOCIETY, DALTON, no. 17, 1972, pages 1911 - 1913 *
SYNTH. REACT. INORG. MET.-ORG. CHEM., vol. 9, no. 6, 1979, pages 565 - 575 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014699A1 (en) * 1993-11-29 1995-06-01 Alliedsignal Inc. Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes
WO1995032240A1 (en) * 1994-05-24 1995-11-30 Alliedsignal Inc. Rtv silicone compositions using aminohydrocarbyl-substituted ketoximinosilanes
US5569750A (en) * 1994-05-24 1996-10-29 Alliedsignal Inc. RTV silicone compositions using aminohydrocarbyl-substituted ketoximinosilanes
KR100252584B1 (ko) * 1994-05-24 2000-04-15 크리스 로저 에이치 아미노히드로카르빌-치환된케톡시이미노실란을이용한실온경화성실리콘조성물

Also Published As

Publication number Publication date
US5405984A (en) 1995-04-11
ES2098058T3 (es) 1997-04-16
EP0660838B1 (en) 1997-03-05
EP0660838A1 (en) 1995-07-05
GR3023562T3 (en) 1997-08-29
JPH07507071A (ja) 1995-08-03
DK0660838T3 (da) 1997-04-28
DE69308579T2 (de) 1997-06-26
DE69308579D1 (de) 1997-04-10
US5359108A (en) 1994-10-25
ATE149500T1 (de) 1997-03-15
JP2554850B2 (ja) 1996-11-20

Similar Documents

Publication Publication Date Title
EP0629648B1 (en) Method for preparation of carbinol-functional siloxanes
US4707531A (en) Method for producing organosilicon polymers and the polymers prepared thereby
US4808664A (en) Moisture curable polyisobutylenes
US20120282210A1 (en) Novel organomodified siloxanes having primary amino functions, novel organomodified siloxanes having quaternary ammonium functions and the method for the production thereof
US3417120A (en) Preparation of organosilicon compounds by reaction of hydrogeno-organosilicon compounds with hydroxyl - group - containing organic compounds
US4552942A (en) Silanes and compositions prepared therefrom
US2909549A (en) Alkoxy-endblocked silicone polymers
EP0660838B1 (en) Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes
US10336866B2 (en) Method for producing organosilicon compounds having amino groups
EP0430216A2 (en) Polydimethylsiloxane terminated at one end by a branched aminoalkyl group and preparation thereof
CA1331011C (en) Polyalkoxysilylalkylenedisilazanes and silylamines
KR100392529B1 (ko) 주석유도체의잠복축중합촉매로서의용도및이것을함유하는예비혼합물
US5605997A (en) Process for producing organopolysiloxanes
US3959327A (en) Organofunctional silicon compounds
US5786493A (en) Cyclic silane esters and solvolysis products thereof, and processes for the preparation of the cyclic silane esters and the solvolysis products
US3183254A (en) Organic silicone compounds and method for producing same
US5514766A (en) Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes
JPS6112931B2 (da)
US5717052A (en) Di-, tri- and tetrafunctional methyl isobutyl and methyl amyl ketoxime-based silanes
US2810628A (en) Method of preparing cyclic polysilox-
US4658006A (en) Method for the preparation of alkoxy-containing organopolysiloxane
US3287291A (en) Diorganosiloxanes cured with an alkoxy end-blocked silyl tetraformal
US5403945A (en) Cyclotrisiloxane and process for producing the same
US5157095A (en) Hydrosilylation of unsaturated aliphatic isocyanates
US3565860A (en) Oxime-containing organotin compounds

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1993921570

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1993921570

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1993921570

Country of ref document: EP